Enantiodivergent syntheses of (+)- and (-)-1-(2,6-dimethylphenoxy)propan-2-ol: A way to access (+)- and (-)-mexiletine from D-(+)-mannitol.
Amine drugs
Chiral pool synthesis
Chiron approach
Common chiral intermediate
D-(+)-mannitol
Enantiodivergent synthesis
Journal
Carbohydrate research
ISSN: 1873-426X
Titre abrégé: Carbohydr Res
Pays: Netherlands
ID NLM: 0043535
Informations de publication
Date de publication:
Jan 2020
Jan 2020
Historique:
received:
10
08
2019
revised:
30
11
2019
accepted:
10
12
2019
pubmed:
7
1
2020
medline:
4
2
2021
entrez:
6
1
2020
Statut:
ppublish
Résumé
Chiron approach was used to acquire optically pure (R)- and (S)-1-(2,6-dimethylphenoxy)propan-2-ol, immediate precursors of (S)- and (R)-mexiletines, respectively. Two different routes were followed from a D-mannitol-derived optically pure common precursor to get the enantiomeric alcohols separately. Comparison of their specific rotation values with the corresponding literature values as well as exact mirror-image relationship between their CD curves proved their high enantiopurity. These alcohols were then transformed to the corresponding amine-drugs in an efficient one-step process instead of two steps described in the literature.
Identifiants
pubmed: 31901892
pii: S0008-6215(19)30478-1
doi: 10.1016/j.carres.2019.107892
pii:
doi:
Substances chimiques
Mexiletine
1U511HHV4Z
Mannitol
3OWL53L36A
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
107892Informations de copyright
Copyright © 2019 Elsevier Ltd. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.